Dan's history with young girls actually goes back to high-school. He was walking home with his best friend Ben, who caught him checking out some pretty grade-school girls. Dan quickly discovered that Ben shared his fascination with little girls and it became a frequent topic for them to fantasize about.
That next summer, Dan was over at Ben's house a lot, since Ben's family had a pool. Ben had a little sister Sue, or Suzi as she was called, who desperately wanted to play with the older boys. She was only 8 and the 15 year old boys really were not interested in her until Dan realized this might be a way for them to fulfill their fantasies.
It was clear that Suzi had a crush on him and with Ben's wholehearted consent, Dan started playing up to Suzi. At first, it was just complements how cute she was; then he would roughhouse with her in the pool, throwing her into the air and copping a feel in the process. When she didn't object, he began telling her how he realized that she was actually pretty sexy and would she like to fool around with him a little.
"What do you mean, fool around?" asked Suzi.
"I'd like to kiss you, that's all" replied Dan. Ben helpfully went inside to make some lemonade and Dan began kissing the little girl. She responded and he pulled her close and began caressing her back, then her butt. Suzi didn't know what to do really, so he suggested that she just wrap her legs around him while they kissed and floated in the water.
Ben watched this eagerly from the kitchen window, confident that Suzi couldn't see him through the glare from the window. After they had been kissing for a while, Dan started playing with her breasts, such as they were. She only had slight pads under her bikini top but her nipples were very sensitive and Dan soon had his hand under her top while he ground his very erect cock into her crotch.
When Ben came out with the lemonade, Dan and Suzi separated quickly, so that Ben might not notice his friend was making out with his little sister. The next day, Dan again made a move on the little girl and she let him touch her all over without any shame, even though Ben was still there. So Dan decided to move things ahead faster than planned and suggested that they both stay in the pool, but get naked.
"But Ben will see!" worried the little girl.
Dan took off his suit and asked her "Can you really see me underwater?"
"I can tell you're naked, but I guess I can't really see details" admitted the little girl.
Dan helped her take off her suit and moved her into the corner of the pool against the wall. He now freely groped her while kissing her intensely. He ground his now free cock against her undeveloped cunt, quickly finding the magic button at the top and making the little girl moan in pleasure. Ben said he had a headache and was going to lie down. He went inside and continued to watch from one of the upstairs windows with a binoculars, so he got a pretty good view of the action. Dan carried Suzi out of the pool, her legs still wrapped around his waist and crotches still grinding together.
"I'm so hot for you" said Dan breathlessly "you are sexier than any of the high school girls I know! I wish you could be my girlfriend!"
"I can be your secret girlfriend" replied Suzi, continuing to hump him on top as they lay on one of the padded benches.
"Do you want to go all the way with me?" asked Dan, kissing her nipples. "It might hurt a little at first but I'm sure you'll enjoy it!"
"OK, but you have to promise to stop if I say so" replied Suzi.
Dan had prepared for this and had some plain coconut oil in his bag with the sun screen and lubed up his hard cock and softly probed the little girls cunt.
"You can be on top and decide how far you want to go" said Dan, rubbing his cock-head back and forth on the little girls pussy. He held his erection vertical and lined it up with Suzi's vagina, then urged her to start sliding down.
Suzi took a deep breath and lowered herself until it started to hurt, then moved up and down a little, getting used to having herself stretched open.
"Are you ready to go down more?" asked the eager boy and the little girl nodded, looking a little scared now. The next time that Suzi moved downward, Dan thrust upward, breaking her cherry, then held the little girl as she cried and moaned softly.
"It's okay! The worst is over. We'll just stay like this until you are ready to move again" said Dan, who reached down and gently stroked the girls clit.
When Suzi felt better, she started moving again and quickly realized that it mostly ached now; the sharp pain had faded and replaced with a full feeling. Dan's fingers on her clit made her feel extra good and quickly Dan and Suzi were fucking in earnest.
Dan was in ecstasy because this was the tightest cunt he'd ever been in and Suzi really was sexy bouncing above him. He quickly took over the movement and was thrusting hard into the little girl who just sort of rode him, feeling overwhelmed with all of the sensations. Dan's climax came unexpectedly for him and he pumped what seemed like gallons of sperm into Suzi.
By this point, Ben was spraying cum on the wall under the windows where he'd been watching this whole act take place. He had to run and get a wet washcloth to clean the wallpaper before it left a stain.
Down by the pool, Dan's erection had not completely faded and he gently humped Suzi, mashing his pelvic bone into her clit, until she too came hard.
Dan fucked Suzi twice more than week, then confessed that Ben had been watching and was incredibly turned on by Suzi as well. After a surprisingly short discussion, Suzi, now very happy to get fucked as often as possible, was also fucking her brother on a regular basis. Suzi admitted that she had had a huge crush on Dan and was happy that he broke her in like that. She also suggested that her best friend Beth had a huge crush on Ben and might be persuaded to join the party.
So, in short order, the two 15 year old boys had two sexy 8 year old girls not just willing but eager to get fucked every day of the week. Since Ben's parents both worked, his house became the hub of sex that summer. Both girls quickly decided they were up for fucking either boy and everyone was happier for it. It may be that Suzi would sometimes sneak into her brother's room at night for another fuck, but no one discussed that.
As much sex as Dan was getting on a regular basis from Suzi and Beth, he was a teenage boy and was not exclusively attracted to little girls. He actually had a girlfriend, by the name of Caroline, and had been fucking her since they started going out together. But even with such an amazing girlfriend, Dan's eye continued to wander towards the younger girls. He hoped she didn't notice this when they walked in the park, for example, and she never said anything to suggest she knew about this side of his psyche.
In the middle of fucking one night, Caroline said "Do you imagine I'm one of those little girls you are always looking at when you fuck me?"
"What are you talking about?" asked Dan, in a panic. "I'm not attracted to little girls!"
"Come on" said Caroline bitterly "Your eyes practically pop out when we're walking in the park and you see a flash of pantie! And the last time we were at Ben's house, I could swear that Suzi was trying to get you alone."
Dan continued to argue his innocence and eventually Caroline said "It's, okay with me, you know. I like little boys and little girls the same way."
Dan didn't know what to say. Caroline asked "Are you actually fucking the 8 year old daughter of your best friend, you dawg!"
"It's not what you think!" argued Dan.
"I've been playing with the twins I babysit since I was 12" admitted Caroline. "I just wish you had been honest with me, that's all."
Caroline had lived next door to the twins Alan and Barry since they were born when she was 6. As they got older, she spent a lot of time acting as a sort of mother's helper, which pleased both her own mother (getting Caroline out of her hair) and the twins mother (who desperately needed the help). By 12, Caroline was trusted to babysit the now nearly 6 year old boys during the day and early evening, since she had her mother just next door as backup.
Caroline started to develop early, so by 12 she had real breasts, though she ignored her mother's insistence that she wear a bra. If there's one thing that will catch the attention of young boys, it's boobies. Caroline had invented a game called "Spelling" where one person would be it, blindfolded and the other two had to write words on that person's body with their fingers. The person being written on had to guess what word it was.
There was no rule at all about where on the blindfolded person's body you could write, so the boys quickly realized they could use this game to touch Caroline wherever they wanted to, then lie about the word they were writing. Since the person who was "it" had to guess the word correctly to win, this meant that frequently the boys would spend seemingly hours touching her entire body. She loved it and was happy to let them probe everywhere.
By the time Caroline turned 13 and could "officially" be a babysitter, she was given the responsibility of putting them to bed as well. She would run a bath for them and generally supervise their washing up. One night, however, the boys were being extra wild and Caroline got completely soaked in the ruckus. Her thin t-shirt and no bra meant her breasts were essentially on display.
"Well, now that I'm soaked" she said "there's hardly any reason for me to keep my shirt on, now is there?
Both boys sat there with open mouths as their pretty babysitter stripped off her shirt and sat there topless.
"You've gotten my shorts all wet, too!" commented Caroline and proceeded to strip those off as well (no underwear of course).
"If you want to act like babies, I'm going to treat you like babies" continued Caroline, who grabbed up the soap and told Alan to stand so she could wash him.
The naked girl lathered her hands and began washing the first little boy's body, paying special attention to his penis (which became hard) and his ass (which she penetrated with her index finger). When he was soaped up well, she told him to rinse and repeated the same with Barry.
Caroline had long been fascinated by the little boys bodies, ever since she helped change their diapers, but playing with their cocks and assholes was a huge amount of fun for her.
After they boys were rinsed, she got them out of the tub and, all three still naked, went into the boys' room to get their PJ's.
"Now, I won't tell your mom you splashed me and made a mess if you are good for me the rest of the night." said Caroline. "Deal?"
Both boys nodded, enraptured by the naked girl in their bedroom.
"Do you want to feel my boobies" asked Caroline and both boys immediately grabbed a boob.
"Not so hard, be gentle with them" said Caroline and proceeded to show them what felt good. Soon enough, both boys were suckling on her nipples as she moaned and rubbed her cunny.
The next time that Caroline babysat and the boys needed a bath, she offered to get in the tub with them, which both boys readily agreed to. This time, it was a mutual soap-fest, with the boys soaping her body up while she soaped up theirs. After the bath, they went into the boys' room and this time, Caroline introduced them to her clit and vagina. The boys were fascinated by the differences between boys and girls. At her suggestion, she sucked on their cocks for a while, then they licked and sucked at her cunt a little.
Over time, Caroline continued further with her sexual explorations with the two boys. By the time she was 14 and they were 8, both boys had graduated to vaginal and anal intercourse with their pretty babysitter. Even though neither boy was old enough to cum, the sensations were wonderful and Caroline came enough for all three of them.
Caroline confronted Suzi the next time they were all at Ben's house.
"I understand you've been fooling around with my boy friend!" said Caroline bitterly.
"He said I could be his secret girlfriend" said Suzi, starting to cry.
Caroline pulled the little girl down next to her and said "Oh, sweetie, don't cry. I really don't mind him fucking you! I think it's the hottest thing I've ever heard."
"Can I please watch Dan fuck you?" asked Caroline, caressing the little girl and kissing her gently.
Dan couldn't believe this turn of events, but being a teen boy, was perfectly happy to fuck anything with a hole that wasn't moving too quickly.
Ben was inside someplace, probably fucking Beth in his bedroom, so Dan pulled off his suit and with Caroline's help took off Suzi's suit and prepared to fuck her.
Caroline stripped nude as well and gave Dan's cock a good sucking "for luck", then lay back and played with her cunt while her boyfriend mounted and fucked the life out of Suzi. Dan was so aroused by this turn of events, that he pounded the little girl relentlessly until she came and then he pulled out and came all over her.
Caroline came over now and gently licked all of the cum off of Suzi, the proceeded to ravish the little girl's cunt with her tongue, making her scream in pleasure.
Of course, this is when Beth came out, shortly followed by Ben. They stared at the mini-orgy taking place outside until Caroline noticed them and said "Jesus, there's another one? Did you just fuck her Ben?"
Ben sheepishly nodded and Caroline announced "I think both of you boys need to fuck me and fuck me right now!" Dan had done anal with Caroline already and he'd regularly watched Dan fuck the two little girls. So a double penetration of his girlfriend with him and his best friend was no big deal.
Suzi and Beth watched as the two hunky teens double fucked the teen girl in front of them. They knew their lives has changed for good and indeed, the rest of the summer and into the fall was a more or less continuous fuck fest.
When Ben, Caroline, and Dan went off to the same college, they continued their shared sex life, finding local girls and boys to add to their collection. Through one little girl, they met Eric, another aficionado of pre-teen girls. Through Eric, they met Frank, and the four men would fuck Caroline together any time they didn't have other alternatives. And between them, they often had a stable of hot pre-teen and tween girls to choose from on any given weekend.
Caroline had even better luck luring young boys into her clutches and Dan realized that he not only didn't mind her fucking boys, he was finding himself attracted to the boys as well. It wasn't just "all assholes feel the same" either; Dan genuinely liked sucking the boys cocks before and especially after they'd fucked Caroline. He enjoyed the few boys who were similarly bi and enjoyed a hard cock in his own ass as a pleasant change.
Dan and Caroline had rented a house (rentals were abundant in a college town like where they were) along with another guy named Jim. Jim was a student as well. He had his own room upstairs; theirs was downstairs. Jim was a bit of a pot head. There was always a haze hanging over the living room or at least it seemed that way.
There were a lot of kids in that neighborhood and of course all the boys, young and old, loved Caroline. So did Jim. The attention he used to pay her never bothered Dan and obviously neither did that of the neighborhood boys. They did it more than a few times, and threesomes were never rare. Caroline used to milk it as much as she could, both with Jim and with the boys.
Caroline used to "doctor" her outfits and strut around: shorts that barely covered her ass and threatened to show her smooth pussy, tops that showed more skin than they covered. And of course, all the boys were around pretty much constantly.
There was a particular group, which would be called 'street kids' these days, who were like a gang almost. No gang colors or anything like that, just a group of the same kids, maybe 7-8 of them. All of the boys were between 11 and 12 years, Caroline's favorite target age. This group used to love hanging out on their front porch, especially in the summertime whenever Caroline was out.
The leader of this band was a boy named Brian. All of them were unkempt, with low income parents who never paid a whole lot of attention to where their kids were or who they were there with. Brian had the long scraggly hair, like most of them, and their clothes were dirty and torn more often than not. Brian made no secret that he had the hots for Caroline. All of them did but he was the recognized leader. She played it up with all the boys but especially with Brian. He wasnt even the oldest, he was one of the 11 year olds but even the older ones deferred to him. He just had that street air of authority about him.
Then there was a girl, Jessie, who was ultra cute in a dirty, raggedy clothing kind of way. Jessie, on the other hand, was almost arrogant. She was definitely aloof. In an unofficial way, she was Brian's girl. She used to stare at Dan, watching him, whenever the clan was gathered, almost with a sneer on her face. She absolutely had a chip on her shoulder. One time when another girl was flirting with Brian, as much as girls that age can flirt. Jessie actually laid a beat down on that girl. But when Dan would catch her staring at him, she would always blush, give a half grin, and turn away. Minutes later, she would be right back to watching him. She never really said much.
So one summer night, they were all out on the porch, Caroline dressed as scantily as she could get away with, when it suddenly started to pour. It was like the floodgates had been opened. Dan and Caroline invited the kids inside, since they weren't about to make them run home in that rain. A couple of them did though. The rest of them went into the living room and sure enough, there was Jim's purple haze hanging in the air. Brian recognized the smell immediately. Jessie did too, she looked at Dan and gave him that half grin that would drive him crazy.
Brian actually asked, all casually, if they had any more dope. Caroline asked him if he really toked and he looked at her like she'd just asked the stupidest question ever. She asked if the rest of them did too and they all answered yes. Being the tease that she was, she asked them sexily if they wanted to get high with her.
Dan was about to jump in and say no, the boys were about to jump Caroline. She was wearing one of those crop tops with the spaghetti straps that never stay up. One or the other of them was always slipping off her shoulder, exposing most of her tit on whichever side the errant strap was. That was the case that night and she had made no effort to correct it. Dan trusted her enough to let things play out; she definitely had a plan in mind.
So, after making sure that they all understood they could never ever tell their parents where they got the weed from, Caroline handed Brian the bag and he proceeded to roll a perfect fattie. That was what Caroline was checking: if the boys couldn't roll, they were lying about getting high. Now as the boys all began to puff up, Jessie, who was sitting right beside Dan on the sofa, looked at him and asked if he was going to get high too. Dan told her he was and she replied 'then so will I.' It was almost the most words she had ever spoken directly to him.
So as they all proceeded to mellow out, Caroline took a long toke, pulled Brian to her, and breathed the smoke directly into his mouth. It was funny, Jessie never seemed to get jealous of Caroline but there she was practically kissing the boy who was supposed to be her bf. It seemed like Brian was going to cum in his jeans and he may well have, Of course all the other boys wanted it the same way and Caroline was only too happy to comply.
When it came to Jessie, she took the joint and started to bring it to her mouth, paused, looked at Dan out of the corner of her eye, and gave him that damn half grin. Only this time she raised her eyebrows as if asking him something. Dan was stoned, they all were, but not so stoned that he didn't know what she was asking. He grinned back at her and gave a slight nod. She took a long toke, straddled his lap, and brought her mouth to his, letting the smoke pass from her mouth to his. Without a word, she threw her arms around his neck, whispered in his ear "I know you like me" and stuffed her tongue in his mouth.
This girl wasn't a terribly experienced kisser but Dan couldn't care less; he loved it. His hands reached behind her and cupped her butt, squeezing her cheeks which made her moan softly into his mouth. Dan managed to pull her hair back and glance across the room to see the boys ripping Caroline's clothes off as she laughed. Jessie had to have felt how hard his cock was beneath her because she started wiggling right on top of it.
She never once looked to see what the boys were doing, she just kept playing tongue wars with him. The boys were dragging a now naked Caroline off to the bedroom, leaving Jessie and Dan alone. She pulled back for a moment, looked at him hesitantly and asked softly if he wanted to fuck her!
Dan had wanted to fuck her since the first moment he saw her walking down the sidewalk in front of our house. That image was so vivid: the torn cutoffs, the dirty tubetop that showed off her new tits wonderfully, her hair long, brown, and scraggly in the breeze. He couldn't take his eyes off her. She had turned her head to look at Dan, gave him that crooked grin for the first time, and walked on by.
Not this night though. This night she had just asked him if he wanted to fuck her! The last thing Dan cared about were the legalities of what they had done getting these kids high, or of what they were about to do. Caroline was getting fucked by 7 or 8 boys, and he was about to carry this dirty little twelve year old street goddess upstairs to Jim's room. He was gone for the night, so no problem there.
That quiet little snarling arrogant vixen was a tiger in bed! Dan didn't think she'd ever fucked a grown man before but she was scratching and growling and just going wild. Her body was absolutely perfect. She had a magnificent bubble butt, hips that wouldn't quit, and the nicest little pair of titties. She was perfect.
Dan was going to fuck her but he was also going to make sure she enjoyed herself. He didn't think anyone had ever gone down on her before because when he did, she timidly asked "I'm not gross down there am I?" He promised her she had the sweetest tasting pussy he had ever tasted. He assured her that she was definitely not gross. That actually got Dan a full on smile. And what a smile it was.
They could hear the boys going wild on Caroline downstairs which is what made Jessie ask with an evil gleam in her eyes, "Am I sweeter than your gf?" Dan smiled back at her and told her yes, she was sweeter, sexier, and hotter than Caroline. With that, she exploded in orgasm. He knew Caroline would understand telling Jessie that, as he'd often heard her tell boys they were hotter than he was. As Jessie came, she threw her arms around his neck, pulled him to her, and kissed him like only someone her age can.
They fucked for hours until he finally had to ask her if her parents weren't going to start to wonder where she was. After all, it was going on 11:00. On the other hand, it was still raining hard outside. He could tell that her parents were the last thing on her mind at the moment. She jolted back to reality and asked what time it was. She asked to use the phone. Not everyone had cell phones back then so it was a landline. Dan thought she was going to call her parents but instead he could tell she was talking to a friend. She was telling her friend that if her parents ever asked, she should tell them that she spent the night at her house.
All that Dan could do was marvel at this naked young girl standing beside the bed. The street light outside came in through the window and illuminated her perfectly. It was almost magical. He heard her telling someone that she was spending the night with someone else and shook himself back to reality. She hung up, looked at him, and asked, again timidly like she was afraid of his answer, if she could spend the night with him, if he wanted.
It struck Dan as the real stupidest question in history. If he wanted her to? Dan grabbed her and pulled her squealing and laughing, back into bed. They made love twice more that night and that phrase 'made love' should be taken seriously. They had finished fucking, now they were making love. She eventually fell asleep in his arms, her head resting on his chest as he stroked her hair. In that moment, Dan wondered if maybe he really did love her. He thought he really did.
Jessie and Dan saw each other a lot over the course of his college days, as did Caroline and the boys. Graduation almost came too soon. Dan had developed a real bond with Jessie and know she felt the same towards him. With Caroline and the boys, it was just sex. It wasn't as hard for them to say good bye as it was for Dan and Jessie.
They stayed in touch at least every other day and more than once she would ask him to help her with homework over the phone. Dan even went back when she asked him if he would take her to her junior prom. This time, she seemed to know a lot more about sex so he knew she hadn't been sitting alone missing him. That knowledge made him both happy and sad. And even after all that time, Dan still hated saying good bye the next day.
After graduation, Dan proposed marriage to Caroline who eagerly accepted. They decided on a civil ceremony, but they started the party early. All of the collected friends fucked Caroline while Dan watched and waited his turn. So as they stood before the judge, Caroline whispered that cum was running down her legs under the dress. Dan almost lost it then, but as soon as the ceremony was over, they went back to the hotel and he quite literally ripped the dress off his new wife, licked every bit of cum he could out of all of her orifices, then fucked her for the first time as a married couple.
Then, of course, all of the other guys fucked her again and again, all night long, until she almost couldn't stand. Dan cleaned her cunt and ass cheerfully, letting his friends celebrate the wedding.
Dan and Caroline's life as a married couple and their two wonderful sons is a story for another time. Six months before meeting Sam and Danni, Caroline was killed by a drunk driver and Dan's life was changed forever.